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The Four Isomeric 1,3,5‐Undecatrienes. Synthesis and configurational assignment
Author(s) -
Näf Ferdinand,
Decorzant René,
Thommen Walter,
Willhalm Bruno,
Ohloff Günther
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580406
Subject(s) - chemistry , reagent , sigmatropic reaction , wittig reaction , stereochemistry , computational chemistry , zinc , combinatorial chemistry , organic chemistry
The four geometrical isomers of 1,3,5‐undecatriene, 1a–d have been prepared (stereospecifically and non‐stereospecifically), using either (1) the Wittig reaction, (2) thermal sigmatropic hydrogen shifts, (3) partial reduction of triple bonds by zinc, or (4) organocopper reagents. The thermal behaviour of the four 1,3,5‐undecatrienes has been investigated and the products formed have been characterized. The spectra of 1a–d, and of related compounds, have been discussed in order to corroborate their configurational assignment.